Madonna's July 1987 Cosmopolitan Cover Story in Full

Cosmopolitan

04-08-2025

Six decades ago, legendary editor Helen Gurley Brown took a stuffy literary magazine and transformed it into an audacious cultural tome. Cosmopolitan has kept evolving since, leading conversations with a sharp, provocative approach that's helped define entire eras of womanhood. One thing that's remained constant: our iconic cover stories, featuring definitive interviews with the leading stars of the time. Join us in revisiting the most classic ones—with their original headlines and exact wording, for better or worse, intact—for a hit of nostalgia and a deep dive into how celebrity has also evolved over the years.
Madonna stands in the lobby of one of New York's fancy East Side hotels. She is a study in black, black jacket, black skirt, black mood. 'I'm here less than twenty-four hours,' she wails, 'and I go running in the Park, and when I get back to my room, my jewelry's gone!'
She seems smaller in person than she looks on film or tape. The skin is porcelain, the eyes as blue as the sapphires that glittered in her stolen bracelet. 'Sean just bought that bracelet for me,' she says, and sighs. 'They took my engagement ring at the last hotel I was at.'
Maybe one day she'll learn to put her valuables in the safe; then again, maybe not. I've heard 'Papa Don't Preach.' I don't want to be the one to tell Madonna what she ought to do. Her husband, the actor Sean Penn, isn't of a mind to lecture her either. Over the phone from Los Angeles (where he's making the film Colors under Dennis Hopper's direction), he promises he'll replace the bracelet. Still, there is more frustration in the offing. Sean reports that nobody will be able to take Madonna's car to the shop. Why not? Because she's got the keys with her.
Later, over lunch, she describes the car. Her husband, the demon giver, bought it for her twenty-seventh birthday. 'It's a white-and-coral fifty-six convertible Thunderbird. Absolutely beautiful.' So why does it have to go into the shop? 'Because,' she says, 'I ran into something while I was talking on the phone.'
A car phone?
She grins. 'Yeah,' she says. 'Kind of disgusting.'
The black mood has passed. Madonna has the gift—and it's one gift her husband didn't buy her—of self-mockery. You can see and hear her laughing at herself on the video version of her 1985 live concert tour. The titles come up on the screen—MADONNA. LIVE. THE VIRGIN TOUR—and over them Madonna chants in a pseudo-Brooklyn accent: 'I went to Noo Yawk...I din know anybody, I wanted to dance, I wanted to sing...I wanted to make people happy, I wanted to be famous, I wanted everybody to love me, I wanted to be a star, I worked very hard and my dream came true.'
The real joke is, her dream did come true. Now she's so famous she can't eat her asparagus without strangers interrupting. Even the staff of the elegant hotel dining room gets into the act. 'The chef would like an autograph for his daughter,' says the maître d'.
'Okay,' Madonna says, 'but you gotta give me a lot of cookies. You know, those really thin wafer cookies?'
The maître d' is amused. 'But the autograph is not for me, it's for the chef.'
'Well, then,' says Madonna, scrawling her name on a piece of paper, 'tell the chef to give me a lot of cookies.'
Dreamer, dancer, singer, actress (coming next month: Who's That Girl with Griffin Dunne), cookie eater, she may just be the biggest star in the entertainment world today. Her first album (Madonna), made in 1983, sold over six million copies, her second (Like a Virgin) sold fourteen million, her third (True Blue) has yielded three number one singles—'Papa Don't Preach,' 'Live to Tell,' and 'Open Your Heart.' She is also the only female vocalist—so far—to have had five number one hits in the eighties. Many people may have been surprised by this. Madonna wasn't one of them.
She is bored with rehashing the old stories, she doesn't want to talk about coming to New York in 1978 with thirty-five dollars in her pocket, she doesn't want to hear how she stepped on the fingers of every man who offered her a hand up on her way to the top. She never, she says, slept with anybody just because he could do something for her. 'Whatever I learned or got from a man or a boyfriend, they got plenty from me. I don't feel like I ever took advantage of anyone.' (This would appear to be true. Steve Bray, a musician she picked up in a disco when she was seventeen, is still writing songs with her, eleven years later.)
That she always had ambition, and that many whom she left behind are resentful, she doesn't deny. 'You can't succeed unless you move,' she says, 'and you can't take the whole world with you.'
She's been moving from the day she was born Madonna Louise Ciccone, in Bay City, Michigan, the oldest girl in a family of six children. Her father was an engineer at Chrysler. When Madonna was six years old, her mother, for whom she was named, died of cancer. When she was eight years old, her father married again. Both of these events infuriated Madonna, who perceived herself as abandoned. She says her mother's death left her with 'a certain kind of loneliness, an incredible longing for something. If I hadn't had that emptiness, I wouldn't have been so driven.'
Needing to be noticed, she made waves. At parochial school, she rebelled against the drab uniforms and flashed bright-colored underpants. In high school, she flirted—stuffing her bra, painting on lipstick an inch thick—and danced, and at seventeen, she won a dance scholarship to the University of Michigan.
But Michigan couldn't hold her. After a few semesters, she headed for New York, where she did some dancing (she was in an Alvin Ailey company), some modeling (the specter came back to haunt her later), and some going hungry. She once said she picked through garbage cans searching for abandoned french fries. It may be true, and if it isn't, who cares? Madonna has always known how to make a good story better. She learned to play several instruments and worked in 'loft and garage bands.' Pure rock didn't satisfy her (she was a disco fanatic, she wanted to make music people would dance to), so she kept moving, searching for the perfect sound.
At one point, she took a side trip to Paris, because a manager said he could make her another Piaf. He couldn't. Or at least he didn't, and Madonna returned to the Apple to begin her real push. She wrote songs, and she recorded tracks—original music on tapes—and took them around to dance clubs and got disc jockeys to play them, while she sang along, live.
'You could almost feel like you were a star, when you were singing to tracks for five thousand screaming maniacs at the Paradise Garage,' says Liz Rosenberg, Madonna's friend, and a Warner Brothers Records vice president. Madonna agrees. 'To me that was the world. That's what I loved, nightclubs and discotheques. And then when the mass audience started catching on to who I was, it was like, Oh, I guess that wasn't the whole world.'
Even after her debut album for Sire Records, it took a year before anybody outside the clubs paid attention. Madonna was not discouraged. She went to David Bowie's record producer and convinced him to produce her second album. She got a part in the movie Desperately Seeking Susan, and she embarked on a twenty-eight-city concert tour. The little girls who came to the shows wore fingerless gloves, crucifixes, and bustiers, and tied their hair with chiffon rags in slavish imitation of their idol.
'They got the humor part of it,' she says. 'For so long, people had been telling girls, 'You have to dress to be nondescript. You have to look masculine if you want to be in control.' And here was someone being sexy and having fun and dressing up and doing exactly what those little girls wanted to do. And making all the decisions, and having power and success.'
That year—1985—Time magazine put Madonna on a cover. The headline read, WHY SHE'S HOT.
Not to be outdone in the heat department, Penthouse and Playboy rushed into print with naked pictures shot back when Madonna (looking more plucked chicken than wanton) scrounged for her supper by posing for 'art' photographers. Then an English magazine, expounding on the fickle nature of popularity, wrote that 'fear and loathing have come very quickly to Madonna.' Had she, in fact, felt loathed?
'Very definitely,' she says. 'The people who adored me were the children who understood where I was coming from. The people who loathed me didn't get it, and my success pissed them off. There's a lot of idiots in the world, and anyway, it makes for more interesting articles. Wouldn't you rather read an article about a slut than a plain-Jane wallflower? I know I would. Anyway, I think it would be kind of boring if everyone really just loved me a hundred percent.'
On August 16, 1985, Madonna married Sean Penn, who loved her a hundred percent, and whose passion for privacy was as fierce as her passion for being cheered in public. Opposites attract, and if a girl who has lived by the maxim 'Hey, look at me!' wants a boy who would just as soon dig a moat around their house, that's their business.
The couple first met on the set where Madonna was making her 'Material Girl' video. 'The director was a friend of Sean's, and she knew that he sort of had a crush on me and she said, 'Hey, I'm working on Madonna's video, do you want to I come and meet her?'
'So I was standing up at the top of these steps, waiting—they were doing some lighting—and I looked down and noticed this guy in a leather jacket and sunglasses kind of standing in the corner, looking at me. And I realized it was Sean Penn, and I immediately had this fantasy that we were going to meet and fall in love and get married. Which is exactly what happened.'
'I came down the steps and walked right by, very cold, I just said, 'Hi.' And he kept hanging around. Hours had gone by, and it had gotten dark, and I saw him poke his head around the corner again, and I was like, Oh, you're still here? So I went outside to talk to him.'
'There were people everywhere, so it was hard for us to have this conversation, but we were just kind of throwing questions at each other and being really provocative. I had given flowers to everybody in the cast and the crew of the video, all the guys, and I had one left. So when Sean was leaving, I said, 'Wait, I have something for you.' And I ran upstairs and I got this rose for him.'
Though it started out romantic, the relationship has had its gritty moments. 'It's a roller coaster,' Madonna says of marriage, and Shanghai Surprise, the movie she and Sean made together, had to be a low point for the honeymooners. They got terrible press, partly because of Sean's penchant for knocking down the odd photographer, partly because critics thought Shanghai Surprise was a lousy movie, and Madonna made a lousy missionary, and she and Sean had no more chemistry between them than two plates of mashed potatoes.
'A hellish nightmare,' is the way Madonna describes the experience. 'I thought it was a great script, and the idea of going to Shanghai was exciting to me, and the idea of working with my husband was exciting to me because he's a great actor. But sometimes everything goes wrong. The director turned out not to know what he was doing, we were on a ship without a captain, and we were so miserable while we were working that I'm sure it shows.
'Some of the tensions were on the set, some were because of the paparazzi. Sean's whole image was sort of blown up into this impossible person out of control. And then when the movie finally got finished—if it was directed poorly, you can't imagine how poorly it was edited. It was a great learning experience, that's all I can say.'
One of the things she learned was never to let herself get into such a situation again. In the record world, she has lots to say about what she—and everyone else on a Madonna record—does, and from now on, she plans to work the same way in the movie business. She says she is not interested in being a tyrant, 'collaborating is what I like,' but she admits she is a very demanding collaborator.
'The musicians yell at me because when they take a meal break, I'm looking at my watch the whole time. 'Okay, thirty minutes is up, get back in the room.' I hate taking breaks, people come back lethargic, the energy's down. I mean, I bring my soy milk and my apple and my rice chips to the studio, and I just want to keep working straight through.'
Having been rendered somewhat cautious by Shanghai Surprise, Madonna didn't leap to say yes when James Foley (who had directed Sean in At Close Range) brought her the script that subsequently became the movie Who's That Girl—a romantic comedy in which she plays a character much like the one in Desperately Seeking Susan. 'I said, 'I like it, but it needs a lot of work.' We went through several writers and several revisions of the script, until it was just the way we wanted.'
Director Foley is convinced Madonna was born to be a movie star. 'The form is big enough, she was made for wide-screen Technicolor. And she is precociously talented. Every time I would say, 'Action!' what she would do made me giggle with excitement. She's very instinctual, what comes out is unencumbered by analysis. Who's That Girl was for me technically difficult, we shot a lot on the streets of New York and L.A., but she helped. Everyone on a crew observes the tone the star sets, and she emanated such a sense of ease and dignity it filtered clear down to the caterer. She's curious as hell too—about lights, scripts, people's names.'
Carol Lees, Madonna's sidekick at Siren Films—Madonna has had her own production company since last June—says her boss works 'forty hours a day. She's got her hands in everything. She'll screen a movie by a director she might want to hire, and if she likes it, we'll have dinner with that director. She complains she has too much work, it's interfering with her career. 'I wish I could get my career going,' she says.
'We have a bungalow—it's all pink-and-purple leopard print—at Universal, where she has a development deal and we look for projects for her to act in and for us to produce together. She's in a special position, she has a little bit of clout because of the success of her music.
'She has an incredibly strong persona, like an old-fashioned movie star, Bette Davis, Katharine Hepburn. I don't think she's going to be like Meryl Streep, German one week, Polish the next.'
But does Madonna look at Meryl Streep and say, 'I could never do that,' or does she say, 'I could do that better'?
'I look at Meryl Streep and I say she's a fine actress,' Madonna says. 'And I'm different. I think I'm a good actress, and I'm going to get better.'
As dopey as she finds the Meryl Streep question, the Marilyn Monroe question irritates her even more. Asked if she thinks of herself as another Marilyn, she bristles, 'If I didn't have blond hair, I don't know what people would do for comparisons.'
But Madonna, dear, didn't you imitate Marilyn in your 'Material Girl' video?
'She's been imitated by a lot of people,' Madonna says. 'Marilyn Monroe was a victim, and I'm not. I know what I'm doing, and what I want. If I make mistakes, or fall into traps, they're mine, not Marilyn Monroe's.'
Guts, you think. She's right when she says she's nothing like Marilyn, who tried to please, to placate, to be loved and, therefore, saved through the grace of some man. Madonna saves herself. Coming to New York as a kid, living in the East Village, going to Paris with strangers, she had no fear.
Wrong, she says. 'I had plenty of fear. Fear was my catalyst. It was the desire to get through all those things—I kept saying, Okay, this is hard, this is scary, but I'm going to make it—that kept me going.'
Is there anything she's still scared of? 'Oh, God, yeah, but it's personal.' She's quiet for a moment. Then: 'The truth scares me,' she says. 'Being alone scares me. Failure scares me. Dying scares me. I don't think in that sense I'm different from anyone else.'
But her life is different from anyone else's. Carol Lees recalls leaving a restaurant one night with Madonna and having a pack of photographers materialize out of the dark, and turn on their floods and flashes. 'There was this white light on her platinum hair and her translucent face, and I have this image of this little vulnerable person, all white face and hair, waving good-bye. Sometimes you'd give your right arm to be Madonna, sometimes, you just want to take her in your arms and say, 'Oh, you poor thing.' At least I can get in my car and not have guys chasing me down the freeway.'
When guys start chasing Madonna down the freeway or anyplace else, her husband, as has been noted, is inclined to fight back. Just last February, he was fined and put on a year's probation for knocking a songwriter off a chair in a nightclub. He thought the songwriter had been trying to kiss Madonna. In April, during a break in the filming of Colors, he punched an extra who had been taking pictures of him and Robert Duvall, which attack caused city prosecutors to issue a warning for Penn's arrest, charging him with violating probation.
Is it fun to have your husband break cameras and whomp strangers while trying to protect you?
'No,' Madonna says, 'It's not fun. But I've been dealing with the media since the very beginning of my career, and Sean never really had to. I wanted it, and I was sort of ready to deal with it and he wasn't. That's all there is to it. I would rather see some sort of harmony taking place than all the violence—and when I say violence, I don't mean necessarily hitting, but people screaming and tugging at you, I don't like any of that.'
Still, she isn't ready to hire an army to shield her from press and public. 'I've just pretty much made up my mind that I'm going to live as normal a life as possible, so I don't go around in limousines, I don't have bodyguards. I like to be pretty low key. I think when you have all that flash sort of stuff, it draws attention to you. When I'm shopping, and people in the stores say, 'Oh, can we have your autograph?' I give them autographs. If I had a bodyguard, the bodyguard would get rid of them, but then he'd follow me everywhere.
'If I'm on tour, or making a movie, and people know where l am, they can bother me, but it's never so much that I feel I can't go on living, or I'm a prisoner. There's a balance. You know, sometimes you get things if you don't have other things.'
The things Madonna does have are considerable. One of them is a Spanish-style villa in a canyon in Malibu surrounded by fifty acres. 'We have a big gate,' she says, 'so it's pretty private, and we have a view of the ocean, and great mountains in the backyard. It's wonderful, but until I got married, I never thought I would live in California, out by the ocean. I mean, I'm from the Midwest. And I lived in New York City for ten years.
'It's great to be up there away from the madness of everything, but then I miss New York. So I come and get a taste of it, get everything stolen, get my nerves racked, get splashed by taxicabs, and then I go back to the nice weather.'
Sean's family also lives in Malibu, where Sean grew up. 'We see his parents probably once a week,' Madonna says. 'They're great. They live right near the ocean, on a big bluff. We bring Hank down there to play with their dog.'
Hank, part wolf, part Akita, is the newest member of the younger Penns' entourage. 'I hate dogs,' Madonna says. 'At least, I hated dogs. But I always have to confront things I hate, walk into things that bother me. And this woman who was doing Griffin Dunne's hair on Who's That Girl told me, 'Oh, my dog just had puppies.' And she's showing everybody pictures, and I saw these little puppies, and they were so cute, and Sean was always saying, 'Oh, I wish we could get a dog.'
'I was always saying, 'No, yuck, I don't want a dog, it's too much responsibility. They pee in the house, and they get dog hair on your clothes.' You know, it's like having a kid, only kids wear diapers, and later on in life they learn how to say decipherable words.'
'But I saw these pictures, and I thought, that would probably be a great thing to do, buy Sean a dog. So I went and picked one out and brought it home to him. I said, 'Come outside, there's somebody out here wants to meet you.' When he saw this dog, he looked like he was going to start crying. Hank is going to be absolutely huge, like a bear, but when we got him, he was a little ball of fur. It was like I'd just had a baby, and Sean saw it and just like died over it. He took it everywhere with him, he wanted to sleep with it, and I was like, uh, what have I done?'
The Penns do not have a large domestic staff. A cleaning lady comes in a couple of times a week, and every once in a while, Madonna finds herself in the laundry room washing clothes, or at the sink. 'I like washing dishes,' she says. 'I have this cleaning impulse sometimes. I think I got it from my stepmother, who cleaned everything in sight all the time.'
The stepmother of whom Madonna was once resentful is now accepted by her; she attributes the improved relationship to her own growing up. 'Ever since I was ten years old, I wanted to leave my house, get out, be my own person. And my father was not at all behind me when I came to New York. To him, it was the unknown, and I had no money and I had no job. And I was angry at him for not being supportive of me, and for a long time, I lost contact with my family.
'I think it's because coming from such a big family, I had to share everything and I wanted to establish my identity and be separate. Now I've grown close to them again, which is great.'
In 1985, Madonna says, her father finally got an idea of what she does for a living. When the Virgin tour came to Detroit, she put him in the act. 'I said, 'Dad, I want you to come on and act like you did when I was little. You want me to get off that stage because you think I'm being naughty. Now really yank me, because I'm going to give you a fight.'
'Well, he came on, and he pulled me so hard, he almost dismembered me. When we got off, I fell down on the floor laughing. But he was completely unfazed by it all. My father is not easily impressed.'
Or shocked, either, one assumes, considering the way his little girl used to take on—and put on—the whole uptight world. She told reporters crucifixes were fun because they had naked men on them—'I thought it was funny,' she says—and she wore safety pins in her pierced ears, and a buckle on her belt that said 'Boy Toy.'
She no longer dresses like that. In the last couple of years, Madonna has changed her style, along with her body. She jogs, she works out, she eats fruits and vegetables—'I've been a vegetarian for years'—and worries her lawyer. 'I had lunch with him, and he's like, 'You've lost weight, my daughter's going to be so upset. You finally gave girls who are voluptuous a new lease on life, don't get any skinnier, okay?''
Foolish lawyer. If Madonna wants to get skinnier, she will get skinnier. Her music won't stay the same, either. 'I'm changing as a songwriter, and as a person. I'm not going to stay the same, and the voice will change too.'
Considering the incredible popularity of the voice, is Madonna miffed that she's never won a Grammy? She says not.
'I don't like those award ceremonies. They're boring, and they don't mean anything. I mean, if you think about the people who get awards, they're not the people I would have thought deserved them. When you come right down to it, pitting people's products against each other, it's so weird. Because everything's good in its own way. If I got an award, I'd probably be really grateful and everything. On the other hand, I don't know.'
Madonna and Sean Penn were married by a priest, which would seem to indicate a serious commitment. ('I think the church pretty much stays with you,' she says. 'Whatever was drilled into you when you were growing up, whatever your picture of God was, I think you die with that image in your head.') Still, right from the start, there have been rumors that the marriage was in trouble—columnist Liz Smith wrote Sean might be 'Sean with the wind'—but if this is the case, Madonna is a genius actress. Because when she speaks of her husband, she sounds like a woman in love. 'I was crazy about him from the beginning,' she says. 'He has the most captivating, intelligent look in his eyes. And he seemed to know so many things about me, we liked so many of the same things, I felt he was my family already.'
Does she worry that it may affect the marriage if she continues to be an enormous star and he, despite the esteem in which his talent is held, continues to work in movies more honored than attended?
'I think the problems that would arise from something like that are inescapable,' she says. 'But I think you learn to deal with insecurity and feeling threatened. I think the longer we're together, and the more we grow to love each other, the more stable we'll feel. And if I start not doing well, or whatever it is that happens, we'll have that basis of strength. I can't say nothing will ever go wrong, but I would hope that ultimately our love would be stronger than anything that happens on the outside.'
Madonna says she and Sean have changed each other. 'I'm an impulsive person, and he thinks about things for a long time. And he broods, and he's very suspicious in a lot of ways, and I'm trusting and gullible. He's made me more tolerant. I think I've helped him to be funny.'
Does Madonna want a baby? 'I would love to have a child,' she says. 'But once I had it, I would probably be very anxious to get back to work.'
When she first blazed on to the music scene, and into the public consciousness, people said she was too hot not to cool down, that she would burn out. She hasn't, but just for the sake of discourse, if everything she's achieved were to disappear tomorrow, would the ride have been worth it?
'Oh, yeah,' she says. 'Definitely.'
July 1987 editor's note: As we go to press, media reports indicate that the Sean Penn–Madonna marriage is over and that Madonna has filed for divorce.